lithium aluminium tetrahydride in tetrahydrofuran

1: 72 percent / butyl-lithium / tetrahydrofuran / 1.5 h / Ambient temperature 2: 63 percent / lithium aluminium hydride / tetrahydrofuran / 12 h / Heating 3: 96 percent / acetic acid; 1,2-dimethoxy-ethane / 0.33 h / Ambient temperature 4: 53 percent / manganese dioxide / CHCl3 / 48 h / Ambient temperature 5: 82 percent / 50percent aq. sodium hydroxide, tetrabutylammonium hydroxide / benzene / 1 h 6: 81 percent / potassium hydrogen carbonate / CHCl3 / 8 h / Heating 7: 69 percent / piperidine / 1.5 h / Ambient temperature 8: 84 percent / lithium aluminium hydride / tetrahydrofuran View Scheme

1: 96 percent / acetic acid; 1,2-dimethoxy-ethane / 0.33 h / Ambient temperature 2: 53 percent / manganese dioxide / CHCl3 / 48 h / Ambient temperature 3: 82 percent / 50percent aq. sodium hydroxide, tetrabutylammonium hydroxide / benzene / 1 h 4: 81 percent / potassium hydrogen carbonate / CHCl3 / 8 h / Heating 5: 69 percent / piperidine / 1.5 h / Ambient temperature 6: 84 percent / lithium aluminium hydride / tetrahydrofuran View Scheme

1: 69 percent / piperidine / 1.5 h / Ambient temperature 2: 84 percent / lithium aluminium hydride / tetrahydrofuran View Scheme